Additionally, while rates aren't historically bad right now, they are higher than 4-5 years ago, and they will be even higher for you as an investor than they were as an owner occupant, which is what you were when you bought originally.I get that you are anxious to add to your portfolio, but that could be achieved without touching your first golden goose.Sometimes on BP, the push is to leverage every last spare penny, but that can be a risky game as the markets shift. 

But if you did the property up right with killer design and great amenities -- I'm picturing cool wallpaper, a game room, boho/modern furniture and a hot tub -- I can see a place here doing well as an affordable Airbnb/STR option just 10 minutes to downtown Denver.

Which they have no skin in the game (Technically).

Real estate is all about learning as you go and playing the long game.

Knowing the laws ahead of time and the process is very important but just know that lateness's are part of the game we play.

I appreciate your plan to do 1031 and get back into the game.

Hey Adam,I’ve been in the Tampa real estate game for 20 years as an investor and owner of a property management company.

I know many of us didn't get into this game until later in life so my hat's off to you.

I am taking your advise, and switched my game plan to include a local agent or property manager to show the properties. 

You already have a pretty solid portfolio, so adding another property and generating more cash flow might accelerate your wealth in a way that the Roth can’t match, especially if you’re planning to transition to real estate full-time soon.The long-term game for you seems to be building that cash flow and equity in real estate, and it sounds like taking the hit on the Roth 401(k) could be worth it for the immediate returns.